Tottenham Hotspur are approaching a familiar crossroads. Ange Postecoglou has made a promising start in his ultimate aim of launching a sustained challenge for the game’s biggest prizes, reinvigorating the squad and reconnecting the club with its long-suffering fan base in a manner reminiscent of two predecessors.
Mauricio Pochettino was the last Tottenham manager to garner genuine affection from Spurs fans even after his sacking in November 2019 — so much so that many wanted him back in the summer before he ended up at Chelsea — but he left amid increasingly public frustration at the club’s failure to act boldly in the transfer market.
Pochettino walked the path previously taken by Harry Redknapp, Spurs’ manager from 2008 to 2012. Redknapp took Tottenham into the modern-day Champions League for the first time in its history in 2010-11 before threatening a Premier League title challenge in the following season, only for the club to opt against his preferred January signings that he believed would sustain their charge. Spurs were just five points off the leaders with 15 games left and Redknapp wanted to acquire forward Carlos Tevez and defender Gary Cahill. Tottenham chairman Daniel Levy opted for cheaper alternatives, bringing in Louis Saha and Ryan Nelsen on free transfers. Tottenham were unable to kick on and Redknapp left the club at the end of the season.
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Postecoglou is still at a formative stage of his tenure but he has already packed a lot in — topping the Premier League table at the start of November before a run of four losses in five games. He will seek further backing next month to help close the gap, asking a question Levy has faced before: are Spurs prepared to be truly aggressive in the market in pursuit of glory?
The experiences of Pochettino and Redknapp are part of a cycle the latter believes Tottenham finally have to break, especially now the new state-of-the-art stadium and training-ground facilities are in place.
“I think if we had bought those couple of players that year, we could have been very close to winning the league with that group,” Redknapp told ESPN. “Pochettino obviously felt something like that after me. People criticise Daniel but the stadium is amazing, the training ground is top drawer.
“They’re building the team now and with everything else in place, hopefully they will be up there challenging every season. But if they want to up there pushing for the top spots like Arsenal are now, they’ve got to move on a little bit, they’ve got to have a bit of a gamble. I can see a similarity with my time for sure.”
Redknapp, 76, was this week announced as the winner of the Outstanding Contribution to London Football prize at the 2024 London Football Awards after spending more than 60 years in the game as a player and manager.
He won the 2008 FA Cup with Portsmouth and earned vital promotions for Bournemouth, Portsmouth and Queens Park Rangers in a managerial career spanning more than 1,300 games but is arguably best remembered for that four-year spell at Tottenham.
Redknapp signed to play for Phoenix Fire in 1980 but the club folded before playing a competitive match. Club owner Leonard Lesser was later found guilty of defrauding investors and sentenced to spend a year at Maricopa County Jail, and Redknapp was left stranded in a motel with his family.
“We started off there in a beautiful hotel but Len was found out, the cheques bounced and suddenly we were in a motel under a motorway, living like something out of [Alfred Hitchcock movie] ‘Psycho.’ It was unbelievable.
“I almost left the game after that. I thought about buying a taxi to become a cabbie but we couldn’t afford to buy one. Thankfully, we got back to England, Bournemouth came along and I got into management.”
Managerial spells at West Ham, Portsmouth, Southampton and then Portsmouth again followed, winning the FA Cup for the first time in Pompey’s history. Redknapp remains the last Englishman to win a major trophy in England but he said: “Probably keeping them up the year before was a bigger achievement.
“To pick up 18 points in the last 10 games and stay in the Premier League with a game to spare was an incredible run. Maybe taking Bournemouth out of the old Third Division [now League One] for the first time in their history in 1987? To win that league will always be special to me. Those achievements took me to Spurs.”
“We had a Christmas do at the end of 2011 and Daniel got up and spoke about me. I remember [first-team coach] Joe Jordan saying to me ‘a lot of people say Daniel doesn’t show his feelings very much but it is amazing, he showed his feelings so much for you today.’ He spoke in such glowing terms in what I’d done and a few months later I lost my job. It was quite strange.”
Redknapp begins to offer a theory that Tottenham owner Joe Lewis was involved. Lewis is widely regarded as being disconnected from day-to-day decision-making, with Levy running the club, but Redknapp said: “I get on well with Daniel. I’ll be honest, I think Joe Lewis would have played a big part in it.
“There was something to do with the team one day — we were playing at Man United. Joe had an opinion about who should play and I had a different opinion. I stuck with my opinion. I just think that had a big part of it but I wouldn’t want to go into it all.”
For much of his career, Redknapp fought the perception he was a “wheeler dealer” rather than a football manager because of a habit of speaking openly about transfers and overseeing significant changes to squads when taking charge.
“I didn’t like that tag all,” he said. “I was a football coach, I understand the game. I’ve lived my whole life watching football from the age of 5, going every week, playing. My dad was a good footballer. Football is my life. I got my coaching badge at 21.
“What happens is, you go to a football club and take over a bad team. That’s why you get the job. So you have to do something about it. The players either aren’t good enough or there’s a problem so you have to change things. If you stick with the same players, you aren’t suddenly going to turn them into a top team. I always tried to treat players right.
“I think you get more out of people telling them what they can do than what they can’t do. In the main, I’ve had that relationship with most of the players I’ve had. There’s always one or two you’ve upset on the way but that’s football.”
